EP2594626B1 - Utilisation d'oxyacétaldéhydes comme parfums sentant le muguet - Google Patents

Utilisation d'oxyacétaldéhydes comme parfums sentant le muguet Download PDF

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Publication number
EP2594626B1
EP2594626B1 EP20110189681 EP11189681A EP2594626B1 EP 2594626 B1 EP2594626 B1 EP 2594626B1 EP 20110189681 EP20110189681 EP 20110189681 EP 11189681 A EP11189681 A EP 11189681A EP 2594626 B1 EP2594626 B1 EP 2594626B1
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Prior art keywords
formula
group
compounds
acetaldehyde
methyl
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EP20110189681
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German (de)
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EP2594626A1 (fr
Inventor
Emilie Singer
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Symrise AG
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Symrise AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/198—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the present invention primarily relates to the use of certain compounds from the group of oxyacetaldehydes as fragrances with a lily-of-the-valley note.
  • the invention relates to mixtures comprising one or more compounds of the formula (I) as defined above and certain compounds of the formula (I) as defined above.
  • Flowery odor compounds are an indispensable component in the fragrance industry as well as in the manufacture of cosmetics, personal care products and detergents and cleaners.
  • a particularly valuable class of these floral fragrances are compounds with a lily-of-the-valley odor note.
  • 3- (4-tert-butylphenyl) -2-methylpropanal (Lilial®, Formula (A)), a synthetic fragrance, has long been one of the most important industrially used fragrances for floral fragrance compositions, particularly with a lily-of-the-valley odor note, and has been used extensively in the cosmetics and soap industries.
  • animal results showed that 3- (4-tert-butylphenyl) -2-methylpropanal could be reprotoxic. It has also been found that this compound may be an allergen and could cause contact dermatitis in sensitive individuals.
  • WO 2004/0769 discloses the use of 4-cyclohexyl-2-butanol as a fragrance, especially as a lily-of-the-valley fragrance.
  • EP 1 857 436 discloses a precursor for aldehyde-type or ketone-type fragrances.
  • fragrances which have additional positive secondary properties beyond their primary, namely, odoriferous properties, such as e.g. a higher stability under certain conditions of use, a higher substantivity and / or diffusivity or a better adhesion, or which by synergy with other fragrances lead to better sensory profiles.
  • odoriferous properties such as e.g. a higher stability under certain conditions of use, a higher substantivity and / or diffusivity or a better adhesion, or which by synergy with other fragrances lead to better sensory profiles.
  • Fragrances that are characterized by the above-mentioned positive secondary properties allow for increased effectiveness in the production of fragrance preparations and perfumed products.
  • the number and the amounts of fragrances in corresponding formulations can be optimized and / or minimized, which leads to a sustainable resource conservation in the production of perfumed products.
  • the primary object of the present invention was to provide suitable compounds for use as a fragrance with a lily-of-the-valley odor note whose odor properties are comparable to 3- (4-tert-butylphenyl) -2-methylpropanal (Lilial®), that is, when using the corresponding Compound as fragrance is to be imparted an odor impression, which largely corresponds to the complexity of the natural odor of the lily-of-the-valley blossom.
  • this fragrance should preferably be superior to the lily-of-the-valley fragrances known from the prior art in terms of the sum of its secondary properties or at least some of its secondary properties.
  • a fragrance in the context of the present text is any substance capable of being used to induce an odor impression, ie to impart an odor impression or to modify (modify or amplify) the odor perception of another substance.
  • This substance in order for it to be used for perfumery purposes, preferably no undesirable side effects, eg health or environmental harmful effects, or the intended use of a product containing this fragrance, have deleterious effects.
  • the compounds of formula (I) may be construed as oxyacetaldehydes in structure.
  • the compounds of the formula (I) as defined above impart an odor impression that comes very close to the complexity of the natural odor of the lily of the valley blossom. That is, the odor impression mediated by the compound of the formula (I) is distinguished, in particular with regard to the lily of the valley note, by outstanding naturalness and complexity.
  • Such a complex largely the natural smell of the lily of the valley flower Odor impression has not been achieved with the known from the prior art fragrances with lily of the valley odor note.
  • the compounds of the formula (I) to be used according to the invention are distinguished by high absorption capacity (inherent adhesion to a substrate) and high substantivity (ability to grow from a, usually aqueous, phase onto a substrate or even after a washing or rinsing process a substrate to remain) from. This effect is particularly evident on substrates such as skin, hair and textile fibers (e.g., wool, cotton, linen, synthetic fibers).
  • fragrances and fragrance preparations are their substantivity to or retention on the substrate, in particular hair or textile fibers.
  • substantially and retention are used eg in EP 1 201 738 A1 explained in detail, compare sections [0004] - [0005]. Fragrances with high substantivity and / or retention are generally sought.
  • a further aspect of the invention relates in particular to the use of the compound of the formula (I) as an agent for increasing the substantivity and / or retention of a fragrance preparation (in particular in relation to or on hair or textile fibers), preferably a fragrance preparation with lily of the valley. Odor note, preferably an odoriferous preparation according to the invention as described below.
  • the compounds of the formula (I) to be used according to the invention are distinguished by their fixing properties, ie they are fixatives.
  • fixatives the compounds of the formula (I) to be used according to the invention increase the adhesive strength of other fragrances, be it by reducing their vapor pressure or adding odor (eg lowering the threshold value).
  • the invention therefore also relates - as already mentioned - the use of the compound of formula (I) as a fixative.
  • compounds of the formula (I) are particularly suitable for imparting, modifying or enhancing a lily of the valley odor note.
  • compounds of the formula (I) in conjunction with one or more other fragrances which are not compounds of the formula (I), in particular with one or more further fragrances, which in turn have a lily of the valley note in are capable of eliciting or enhancing further odor notes and impressions desired for perfumery purposes, in particular odor notes selected from the group consisting of flowery (see Examples 4, 5 and 7), fruity (see Example 10), aqueous (see Examples 5 and 10), green (see Examples 8 and 9) and aldehyde (see Example 6) and / or impressions selected from the group consisting of natural (see Examples 4, 6-8), fresh (see Examples 5 and 11), caring ( see example 5), gentle (see example 9), warm (see example 9), complex and bright.
  • the compound of the formula (Ia) as defined above is distinguished by an odor profile comprising the odor notes of green, flowers (in particular lily of the valley and jasmine), fruit (in particular banana) and the impressions natural and fresh.
  • the compound of the formula (Ib) as defined above is distinguished by an odor profile comprising the odor notes aldehyde, flower, in particular lily-of-the-valley (in a complexity which is particularly similar to the odor of 3- (4-tert-butylphenyl) -2-methylpropanal (Lilial)), green and powdery as well as the impressions warm and gentle.
  • the compound of the formula (Ib) is particularly preferred according to the invention, since its odor profile comprises all essential odor aspects of the compound 3- (4-tert-butylphenyl) -2-methylpropanal, including, in particular, the powdery odor note of the lilial hardly to be reproduced by other fragrances.
  • this compound is particularly well suited to replace 3- (4-tert-butylphenyl) -2-methylpropanal.
  • the compound of the formula (Ic) as defined above is distinguished by an odor profile comprising the odor notes bloom, in particular lily of the valley, green, watery (aquatic).
  • the compound of the formula (Id) as defined above is distinguished by the olfactory note bloom, in particular lily of the valley.
  • the compound of the formula (Ie) as defined above is distinguished by an odor profile comprising the odor notes aldehydig and bloom (especially lily of the valley).
  • the present invention also provides a compound of the formula (I) as defined in claim 6.
  • the compound of the formula (I) according to the invention is particularly preferred.
  • the present invention also provides the compound 1- (2,2-diethoxyethoxy) -4-isopropylcyclohexane (formula (IIb) which is a precursor of the compound 2- (4-isopropylcyclohexyloxy) acetaldehyde (Formula (Ib)) (see Examples 1 and 3).
  • the total amount of the compounds of the formula (I) as defined above is in the range from 0.0001 to 40% by weight, preferably in the range from 0.001 to 25% by weight, in each case based on the total weight of the mixture ,
  • fragrance mixtures Such mixtures according to the invention are also referred to below as fragrance mixtures or fragrance preparations.
  • a typical form of fragrance preparations are perfume oils.
  • one or more compounds of the formula (I) as defined above preferably in one of the preferred embodiments, with one or more other fragrances (preferably with one, several or all odor notes selected from the group consisting of flowery, aqueous, fruity, green, aldehydic), which are not compounds of the formula (I), mixtures with particularly interesting, natural, new and original notes can be created.
  • one or more compounds of the formula (I) with one or more further fragrances, which in turn have a lily-of-the-valley note, but are not compounds of the formula (I).
  • Fragrances which are suitable for the purposes of the above definition as further fragrances for use in a mixture according to the invention are found, for. In S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published , or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001 ,
  • Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balsams, tinctures such.
  • Citronellal Citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of Geranial, Neral, the cyclic terpene alcohols such.
  • allyl-3-cyclohexylpropionate Allylcyclohexyloxyacetat; cis- and trans-methyldihydrojasmonate; cis- and trans-methyl jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene-carboxylate; Ethyl-2-methyl-1,3-dioxolan-2-acetate; the araliphatic alcohols such as benzyl alcohol; 1-phenylethyl; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phen
  • such a mixture according to the invention optionally contains further constituents which themselves are not fragrances within the meaning of the above definition, such as e.g. Solvents, solubilizers, emulsifiers, stabilizers, radical scavengers.
  • a mixture according to the invention in particular in the form of a perfume oil, comprises one, 2, 3 or more further fragrances with a lily-of-the-valley odor note and optionally one, several or all odor notes selected from the group consisting of flowery, fruity, green, aqueous and aldehyde.
  • Corresponding fragrances are known to the person skilled in the art.
  • the total amount of the compounds of the formula (I) as defined above is in the range from 0.0001 to 40% by weight, preferably in the range from 0.0001 to 40% by weight Range from 0.001 to 25 wt .-%, each based on the total weight of the mixture.
  • Solvents selected from the group consisting of the trialkyl citrates, the dialkyl phthalates, benzyl benzoate, isopropyl myristate, and dioctyl adipate are preferred solvents for the compound of formula (I) because, in contrast to other solvents conventionally used in perfumed products (see below), e.g. Dipropylene glycol does not lead to a reduction in the intensity of the lily-of-the-valley note (see also Example 27).
  • solvent or one of the solvents is selected from the group consisting of triethyl citrate, diethyl phthalate, benzyl benzoate, isopropyl myristate and dioctyl adipate.
  • Mixtures consisting of (i) a solvent from the group consisting of triethyl citrate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, benzyl benzoate and isopropyl myristate and (ii) one or both compounds from the group consisting of phenoxyacetaldehyde and p-methylphenoxyacetaldehyde are not preferred.
  • a mixture according to the invention contains, besides one or more further compounds of formula (I) (as defined above) and / or one or more further solvents from the group consisting of the trialkyl citrates (with the exception of triethyl citrate) and Dioctyladipat contains.
  • a mixture of the invention containing one or more compounds of formula (I) and one or more solvents selected from the group consisting of the trialkyl citrates, the dialkyl phthalates, benzyl benzoate, isopropyl myristate, and dioctyl adipate does not comprise a compound selected from the group consisting of from phenoxyacetaldehyde and p-methylphenoxyacetaldehyde.
  • the compounds of the formula (I) to be used according to the invention and mixtures according to the invention which contain one or more compounds of the formula (I) and one or more solvents from the trialkyl citrate group and also fragrance preparations according to the invention as defined above are used in particular for the preparation of perfumed products (perfumed Article).
  • perfumed products thus represent a third group of mixtures according to the invention.
  • the mixture according to the invention is preferably a perfumed product selected from the group consisting of detergents and cleaners, hygiene or care products, in particular from the field of body and hair care, cosmetics and household items, fine fragrances (perfumes), air care products (especially candles), air fresheners, cleaning, treating and / or caring surfaces and textile fibers.
  • the total amount of the compounds of formula (I) as defined above is in the range of 0.0001 to 5 wt .-%, preferably in the range from 0.001 to 2.5 wt .-%, each based on the total weight of the product.
  • Fragrance preparations according to the invention comprising the compound of the formula (I) or a mixture according to the invention as defined above can be used in general (for example in concentrated form, in solutions or in modified form described below) for the preparation of, for example, perfume extracts, Eau de perfumes, Eau de Toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes and scented refreshing wipes and the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bath and sanitary cleaners, scouring cream, solid and liquid Toilet cleaners, powder and foam carpet cleaners, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soak and stain removers, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel-like or solid-applied form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe polishes
  • Preferred perfumed products according to the invention are products selected from the group consisting of detergents and cleaners, hygiene or care products, in particular from the field of body and hair care, cosmetics and household, fine fragrances (perfumes), air care products (especially candles ), Air fresheners.
  • fragrance preparations according to the invention or the fragrance preparations to be used according to the invention in the corresponding products can be used in liquid form, undiluted or diluted with a solvent for perfuming.
  • suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, trialkyl citrates, in particular triethyl citrate, isopropyl myristate, etc.
  • solvents mentioned explicitly these are used in the context of the present text in the case of the presence of their own olfactory properties exclusively belong to the component "solvent" and not to the "fragrances”.
  • the compound (s) of the formula (I) or the mixture according to the invention of the first or second group (as defined above) contained in the perfumed products according to the invention may in a preferred embodiment be absorbed on a carrier which provides both a fine distribution of the fragrances in the product and a controlled release in the application.
  • a carrier which provides both a fine distribution of the fragrances in the product and a controlled release in the application.
  • Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as woods and cellulosic based materials.
  • the compound (s) of the formula (I) or the mixture according to the invention of the first or second group (as defined above) present in the perfumed products according to the invention can also be microencapsulated, spray-dried, as inclusion complexes or are present as extruded products and are added in this form to the product or article to be perfumed.
  • the properties of the thus modified mixtures can be further optimized by so-called “coating” with suitable materials with a view to a more targeted release of fragrance, for which preferably wax-like plastics such as e.g. Polyvinyl alcohol can be used.
  • the microencapsulation of the fragrance preparations can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be prepared, for example, by spray-drying an emulsion or dispersion containing the perfume oil, it being possible to use as excipients modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can be e.g. by incorporating dispersions of the fragrance preparation and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • Extrusion products can be made by fusing the fragrance preparation with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol, done.
  • the compound (s) of the formula (I) or the mixtures of the first or second group (as defined above) to be used according to the invention can accordingly, as already mentioned, be in concentrated form, in solutions or in the modified form described above be used for the preparation of the corresponding products of the invention.
  • Ingredients with which the compound of the formula (I) according to the invention or the mixture according to the invention of the first or second group (as defined above) may preferably be combined are, for example: preservatives, abrasives, anti-acne agents, anti-aging agents, antibacterial agents, anti-cellulites Agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, anti-irritants, antimicrobials, antioxidants, astringents, antiperspirants Antiseptics, antistatics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, skin care agents, depilatory agents, surface-active substances, deodorizing agents, antiperspirants, emollients, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foaming agents, Foam stabilizers, foam inhibitors, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair styling agents, hair straightening
  • the high substantivity of the compounds of the formula (I) to be used according to the invention proves advantageous, because the higher the substantivity of a fragrance, the lower the amount of fragrance required to maintain an odor over a certain time.
  • the batch is mixed with 50 mL of saturated ammonium chloride solution and 50 mL of water.
  • the aqueous phase is extracted three times with 150 ml of ethyl acetate and the combined organic phases are washed twice with 50 ml of saturated sodium chloride solution washed.
  • the crude product (52.0 g, 70%, 65% of theory) is purified by distillation. 21 g of 1- (2,2-diethoxyethoxy) -3-methylbutane are isolated in 96% purity. This corresponds to a yield of 37% of theory.
  • the aqueous phase is extracted four times with 100 ml of diethyl ether and the combined organic phases are washed with 100 ml of sodium hydroxide solution, four times with 100 ml of water and 100 ml of saturated sodium carbonate solution. After removal of the solvent, 40.3 g of 1- (2,2-diethoxyethoxy) -4-isopropylbenzene are obtained in 97% purity. This corresponds to a yield of 84% of theory.
  • Perfume oil A1 (comparison) Perfume oil A2 (according to the invention) ETHYL ACETOACETATE 4.0 4.0 HEXENOL CIS-3 10% DPG 3.0 3.0 HEXENYL ACETATE CIS-3 10% DPG 3.0 3.0 HEXENYL BENZOATE CIS-3 10% DPG 3.0 3.0 VERTOCITRAL 10% DPG 5.0 5.0 CYCLOGALBANAT® 10% DPG 3.0 3.0 STYRALYL ACETATE 10% DPG 6.0 6.0 BERGAMOT OIL BERGAPTEN FREE FF 6.0 6.0 MANDARIN OIL DIST.
  • Perfume oil B1 (comparison) Perfume oil B2 (according to the invention) NONADIENAL TRANS, CIS-2.6 5% TEC 20% DPG 2.0 2.0 ETHYL ACETOACETATE 3.0 3.0 FARENAL® 10% DPG 5.0 5.0 VERTOCITRAL 3.0 3.0 CYCLOGALBANAT® 10% DPG 2.0 2.0 STYRALYL ACETATE 3.0 3.0 MELONAL® 0.5 0.5 DIHYDRO MYRCENOL 15.0 15.0 LINALYL ACETATE 20.0 20.0 LEMON OIL TERPENES FLAVOR WONF 8.0 8.0 EUCALYPTOL NAT.
  • Perfume oil C1 Perfume oil C2 (according to the invention)
  • ALDEHYDE C10 0.5 0.5 ALDEHYDE C11 ISO 2.0 2.0 ALDEHYDE C11 UNDECYLENIC 12.0 12.0 ALDEHYDE C12 MNA 6.0 6.0 FARENAL® 1.0 1.0 VERTOCITRAL 8.0 8.0 ALLYL AMYL GLYCOLATE 1.0 1.0 STYRALYL ACETATE 1.5 1.5 DIHYDRO MYRCENOL 65.0 65.0 AGRUNITRIL 1.0 1.0 PEONILE 15.0 15.0 METHYL ANTHRANILATE 10.0 10.0 NEROLIONE 10% DPG 1.5 1.5 ROSEMARY OIL BM 7.0 7.0 SAGE OFFICINAL OIL DALM.
  • Perfume oil D1 Perfume oil D2 (according to the invention)
  • ALDEHYDE C8 10.0 10.0
  • ALDEHYDE C10 14.0
  • ALDEHYDE C11 UNDECYLIC 5.0
  • ALDEHYDE C12 MNA 4.0
  • ISOAMYL ALCOHOL 6.0 VERTOCITRAL 4.0
  • ALLYL AMYL GLYCOLATE 4.0 DIHYDRO MYRCENOL 120.0 120.0 CITRAL 95 30.0 30.0 AGRUNITRIL 80.0 80.0 CITRONITRILE 40.0 40.0 CITRYLAL 4.0 4.0
  • Perfume oil E1 (comparison) Perfume oil E2 (according to the invention)
  • ALDEHYDE 8 0.5 0.5 HEXENOL CIS-3 3.5 3.5 VERTOCITRAL 15.0 15.0 STYRALYL ACETATE 3.0 3.0 MELONAL® 2.0 2.0 DIHYDRO MYRCENOL 60.0 60.0 CITRAL 95 6.0 6.0
  • the proportion of 2- (3-methylbutoxy) acetaldehyde (formula (Ia)) in perfume oil E2 causes an enhancement of the green notes. Furthermore, the composition radiates with 2 (3-methylbutoxy) acetaldehyde overall more naturalness.
  • Perfume oil F1 Perfume oil F2 (according to the invention)
  • ALDEHYDE C10 0.5 0.5 ALCOHOL C10 6.0 6.0 HEXENOL CIS-3 1.0 1.0 limonenal 4.0 4.0 VERTOCITRAL 8.0 8.0 PHENYLACETALDEHYDE 50% DPG 1.0 1.0 MINTONAT 15.5 15.5 METHYL ANTHRANILATE 1.0 1.0 HEXYL ACETATE 20.0 20.0 ALLYL HEPTOATE 1.0 1.0 LINALOOL 30.0 30.0 DIMETHYL BENZYL CARBINYL ACETATE 2.0 2.0 PHENYLETHYL ALCOHOL 150.0 150.0 CITRONELLOL 950 130.0 130.0 GERANIOL SUPER 35.0 35.0 GERANYL ACETATE PURE 10.0 10.0 BENZYL ACETATE 55.0 55.0 HEDIONE 15.0 15.0 HEXYL CINNAMIC ALDEHYDE ALPHA 130.0 13
  • Perfume oil G1 Perfume oil G2 (according to the invention)
  • Perfume oil G2 FARENAL® 3.0 3.0 FLORAZON 0.5 0.5 HEXENYL ACETATE CIS-3 3.0 3.0 VERTOCITRAL 1.0 1.0 DYNASCONE 10% DPG 2.0 2.0 CYCLOGALBANAT® 2.0 2.0 STYRALYL ACETATE 1.5 1.5 DIHYDRO MYRCENOL 6.0 6.0 OXANTHIA 50% IN TEC 10% DPG 10.0 10.0 LEMON OIL ITAL.
  • Example 12 Transparent deodorant sticks (formulation A, B) or deodorant cream sticks (formulation C, D)
  • Perfume oil H1 (comparative) Perfume oil H2 (according to the invention)
  • ALDEHYDE C10 0.5 0.5 ALDEHYDE C12 MNA 10% DPG 2.0 2.0 MINTONAT 40.0 40.0 MELOZONE 0.5 0.5 VERTOCITRAL 6.0 6.0 DIHYDRO MYRCENOL 120.0 120.0 TETRAHYDRO MYRCENOL 10.0 10.0 AGRUNITRIL 1.0 1.0 ORANGE OIL BRASIL 10.0 10.0 TAMARINE TYPE BASE 10.0 10.0 HEXYL ACETATE 6.0 6.0 ALDEHYDE C14 SO-CALLED 1.0 1.0 TETRAHYDRO LINALOOL 40.0 40.0 DIMETHYL BENZYL CARBINYL BUTYRATE 5.0 5.0 ORANGE FLOWER ETHER 5.0 5.0 PHENYLETHYL ACETATE 6.5 6.5 PHENYLETHYL ALCOHOL 15.0 15.0 GERANIOL SUPER 30.0 30.0 ROSAPHEN
  • the mixture obtained after mixing together the specified components is filled with a propane-butane mixture (2: 7) in a weight ratio of 2: 3 in an aerosol container.
  • Example 16 hair conditioner with UV protection
  • part raw materials INCI name Wt .-% A Water, demineralized Water (aqua) 69,50 glycerin glycerin 4.00 1,3 butylene glycol Butylene glycol 5.00 D-panthenol panthenol 0.50 Lara Care A-200 Galactoarabinan 0.25 B Baysilone oil M 10 Dimethicone 1.00 Edeta BD Disodium EDTA 0.10 Copherol 1250 Tocopheryl acetate 0.50 Cetiol OE Dicaprylyl ether 3.00 Neo Heliopan ® HMS Homosalate 5.00 Neo Heliopan ® AV Ethylhexyl methoxycinnamate 6.00 Neo Heliopan ® 357 Butyl methoxydibenzoylmethane 1.00 Corapan TQ Diethylhexylnaphthalate 2.00 Alpha bisabolol bisabolol 0.10 Pemulen TR-2 Acrylates / C10-30 Alkyl Acrylate
  • Method of preparation Dissolve Lara Care A-200 with stirring in the other components of Part A. Weigh all raw materials of part B (without pemulen) and dissolve the crystalline substances by heating. Disperse pemulen. Add part B to part A and homogenize for 1 minute. Add parts C-E and homogenize with the Ultra Turrax for another 1-2 minutes.
  • the hair coloring base (part A) according to the invention and the developer according to the invention (part B) are stirred together in a weight ratio of 1: 1 ratio and applied to the hair.
  • Example 21 Hair dye cream for a blonde tint
  • Method of preparation Mix together parts A, B and C except Covaquat 16 and heat at 80 ° C for 20 minutes. After the product is homogeneous, allow to cool. Add Covaquat 16 at 50 ° C. When the product starts thickening stop the stirring. NH 4 OH is added at room temperature and the mixture is stirred until homogenization.
  • Example 22 Air Freshener Aerosol Spray, Water Based (w / o Alcohol)
  • Method of preparation Mix all raw materials together in the order listed.
  • Method of preparation Mix all raw materials together in the order listed. Adjust pH.
  • Example 24 deodorizing air freshener pump / wick 5% fragrance
  • Method of preparation Mix together the materials of Part A in the order listed. Mix materials of part B together. If part A is clear, add part B. Then add part C and stir until the mixture is homogeneous.
  • Method of production Melt the candle wax and stir. Add the perfume oil, stir well. Pour into the desired shape.
  • Example 26 WC stone
  • Method of preparation let part A melt. Mix part B using a mixing mixer. In the extruder at 35-40 ° C to form a toilet block.
  • the intensity test is a test for determining the sensory strength of a substance on smelling strips.
  • 2- (3-methylbutoxy) acetaldehyde (formula (Ia)) is selected in the form of a 50% strength by weight solution in a solvent from the group consisting of triethyl citrate (TEC), diethyl phthalate (DEP), benzyl benzoate, isopropyl myristate (IPM) , Dioctyl adipate (DOA) and dipropylene glycol (DPG) each dipped on an encoded smelling strip, and from a panel of probands (5 or more persons), the intensity of the lily of the valley smelling note is scored on a scale from 1 (odorless) to 9 (very strong). From the individual measured values, mean values are calculated, which are rounded to whole numbers.
  • TEC triethyl citrate
  • DEP diethyl phthalate
  • IPM isopropyl myristate
  • DOA Dioctyl adipate
  • DPG dipropylene glycol
  • TEC triethyl citrate
  • DEP diethyl phthalate
  • IPM isopropyl myristate
  • DOA dioctyl adipate
  • DPG dipropylene glycol
  • Triethyl citrate 1 Dipropylene glycol (DPG) 1 Diethyl phthalate (DEP) 1 benzyl benzoate 1 Isopropyl myristate (IPM) 1 Dioctyl adipate (DOA) 1 2- (3-methylbutoxy) acetaldehyde (Formula (Ia)) 50% in DPG 3 2- (3-methylbutoxy) acetaldehyde (formula (Ia)) 50% in TEC 6 2- (3-methylbutoxy) acetaldehyde (Formula (Ia)) 50% in DEP 5 2- (3-methylbutoxy) acetaldehyde (formula (Ia)) 50% in benzyl benzoate 5 2- (3-methylbutoxy) acetaldehyde (Formula (Ia)) 50% in (IPM) 5 2- (3-methylbutoxy) acetaldehyde (formula)) 50% in benzyl benzoate 5 2- (3-methylbutoxy)

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Claims (14)

  1. Utilisation d'un composé de la formule (I) ou d'un mélange contenant un ou plusieurs composés de la formule (I) ou d'un mélange se composant de deux ou de plusieurs composés de la formule (I),
    Figure imgb0108
     dans laquelle vaut :
    n est 0 ou 1, où
    (i) si n = 1
    les deux paires d'une ligne continue et d'une ligne en traits interrompus dans la formule (I) représentent chacune des liaisons simples
    et
    a) R1 et R2 représentent chacun un groupe alkyle saturé non-ramifié, le nombre total des atomes de carbone dans les groupes R1 et R2 étant compris entre 4 et 9
    ou
    b) R1 et R2 forment conjointement avec l'atome de carbone disposé entre eux un cycle cyclohexyle
    Figure imgb0109
     où la ligne en traits interrompus représente la liaison qui lie le cycle cyclohexyle à l'atome d'oxygène voisin dans la formule (I), et
    où R3, R4 et R5 sont choisis, indépendamment les uns des autres, dans le groupe constitué par l'hydrogène, le méthyle, l'éthyle, l'isopropyle et le tert-butyle, et le nombre total des atomes de carbone du cycle cyclohexyle et des groupes R3, R4 et R5 est compris entre 6 et 10
    ou
    c) R1 est de l'hydrogène et R2
    c1) est un groupe alkyle saturé ramifié ayant 4 à 9 atomes de carbone
    ou
    c2) est un cycle cyclohexyle
    Figure imgb0110
     où la ligne en traits interrompus représente la liaison qui lie le cycle cyclohexyle à l'atome de carbone voisin dans la formule (I), et
    où R3, R4 et R5 sont choisis, indépendamment les uns des autres, dans le groupe constitué par l'hydrogène, le méthyle, l'éthyle et l'isopropyle, et le nombre total des atomes de carbone du cycle cyclohexyle et des groupes R3, R4 et R5 est compris entre 6 et 9
    ou
    c3) est un cycle phényle
    Figure imgb0111
    où la ligne en traits interrompus représente la liaison qui lie le cycle phényle à l'atome de carbone voisin dans la formule (I), et
    où R3, R4 et R5 sont choisis, indépendamment les uns des autres, dans le groupe constitué par l'hydrogène, le méthyle, l'éthyle et l'isopropyle, et le nombre total des atomes de carbone du cycle phényle et des groupes R3, R4 et R5 est compris entre 6 et 9
    et
    (ii) si n = 0
    les deux paires d'une ligne continue et d'une ligne en traits interrompus dans la formule (I) représentent chacune des liaisons aromatiques
    et
    (d) R1 et R2 forment conjointement avec l'atome de carbone disposé entre eux un cycle phényle
    Figure imgb0112
    où la ligne en traits interrompus représente la liaison qui lie le cycle phényle à l'atome d'oxygène voisin dans la formule (I), et
    où R3, R4 et R5 sont choisis, indépendamment les uns des autres, dans le groupe constitué par l'hydrogène, le méthyle, l'éthyle, l'isopropyle et le tert-butyle, et le nombre total des atomes de carbone du cycle phényle et des groupes R3, R4 et R5 est compris entre 6 et 10,
    ou d'un composé choisi dans le groupe constitué par
    3.) le 2-(1,1-diméthylpropoxy)acétaldéhyde
    Figure imgb0113
    4.) le 2-(1,3-diméthylbutoxy)acétaldéhyde
    Figure imgb0114
    6.) le 2-[(1,5-diméthylhexyl)oxy]acétaldéhyde
    Figure imgb0115
    7.) le 2-(1,1-diméthylhexoxy)acétaldéhyde
    Figure imgb0116
    8.) le 2-[(2-éthylhexyl)oxy]acétaldéhyde
    Figure imgb0117
    - en tant que substance odoriférante ayant une note de muguet et/ou
    - comme agent destiné à augmenter la substantivité et/ou la rétention d'une préparation de substance odoriférante
    et/ou
    - en tant que fixateur.
  2. Utilisation selon la revendication 1, dans laquelle
    un ou plusieurs composés de la formule (I) tels que définis dans la revendication 1 sont utilisés pour conférer, modifier ou renforcer une note olfactive de muguet et
    (i) une, plusieurs ou toutes les notes olfactives choisies dans le groupe constitué par fleurie, fruitée, aqueuse, verte et aldéhyde
    et/ou
    (ii) une, plusieurs ou toutes les impressions choisies dans le groupe constitué par naturelle, fraîche, de soin, douce, chaude, complexe et rayonnante.
  3. Utilisation selon la revendication 1 ou 2, caractérisée par le fait que le composé utilisé de la formule (I) ou un, plusieurs ou tous les composés de la formule (I) dans le mélange utilisé sont choisis dans le groupe constitué par des composés dans lesquels
    - n = 1, R1 est de l'hydrogène et R2 est un groupe alkyle saturé ramifié
    Figure imgb0118
     avec, dans l'ensemble, 4 à 9 atomes de carbone, où R6 est un groupe alkyle saturé ramifié ou non-ramifié ayant 1 à 6 atomes de carbone et la ligne en traits interrompus représente la liaison qui lie le groupe alkyle saturé ramifié R2 à l'atome de carbone voisin dans la formule (I), ou
    - n = 1 et R1 et R2 forment conjointement avec l'atome de carbone disposé entre eux un cycle cyclohexyle comme défini ci-dessus, R3 et R5 sont de l'hydrogène et R4 est choisi dans le groupe constitué par le méthyle, l'éthyle et l'isopropyle et le tert-butyle, ou
    - n = 0 et R1 et R2 forment conjointement avec l'atome de carbone disposé entre eux un cycle phényle comme défini ci-dessus, R3 et R5 sont de l'hydrogène et R4 est choisi dans le groupe constitué par le méthyle, l'éthyle et l'isopropyle et le tert-butyle, ou
    - n = 1, R1 est le méthyle et R2 est un groupe alkyle saturé non-ramifié ayant 4 à 6 atomes de carbone.
  4. Utilisation selon la revendication 1 ou 2, caractérisée par le fait que le composé utilisé de la formule (I) ou un, plusieurs ou tous les composés de la formule (I) dans le mélange utilisé sont choisis dans le groupe constitué par des composés dans lesquels
    - n = 1, R1 est de l'hydrogène et R2 est un groupe alkyle saturé ramifié
    Figure imgb0119
     avec, dans l'ensemble, 4 à 9 atomes de carbone, où R6 est un groupe alkyle saturé ramifié ou non-ramifié ayant 1 à 6 atomes de carbone et la ligne en traits interrompus représente la liaison qui lie le groupe alkyle saturé ramifié R2 à l'atome de carbone voisin dans la formule (I), ou
    - n = 1, R1 est le méthyle et R2 est un groupe alkyle saturé non-ramifié ayant 4 à 6 atomes de carbone.
  5. Utilisation selon l'une quelconque des revendications 1 à 3, caractérisée par le fait que le composé utilisé de la formule (I) ou un, plusieurs ou tous les composés de la formule (I) dans le mélange utilisé sont choisis dans le groupe constitué par le
    - 2-(3-méthylbutoxy)acétaldéhyde (formule (la)) (2-isopentyloxy acétaldéhyde)
    Figure imgb0120
    - 2-(4-isopropylcyclohexyloxy)acétaldéhyde (formule (Ib))
    Figure imgb0121
    - 2-(4-isopropylphénoxy)acétaldéhyde (formule (Ic))
    Figure imgb0122
    - 2-(3,5,5-triméthylhexoxy)acétaldéhyde (formule (Id))
    Figure imgb0123
    - 2-[(1-méthylheptyl)oxy]acétaldéhyde (formule (Ie))
    Figure imgb0124
  6. Composé choisi dans le groupe constitué par :
    le 2-(4-isopropylcyclohexyloxy)acétaldéhyde (formule (Ib))
    Figure imgb0125
     et
    le 2-(3,5,5-triméthylhexoxy)acétaldéhyde (formule (Id))
    Figure imgb0126
  7. 1-(2,2-diéthoxyéthoxy)-4-isopropylcyclohexane (formule (IIb)
    Figure imgb0127
  8. Mélange contenant un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes, de préférence un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications 3 à 5,
    dans lequel le mélange
    - contient une, 2, 3, 4, 5, 6, 7, 8, 9, 10 autres substances odoriférantes ou plus qui ne sont pas de composés de la formule (I),
    et/ou
    - contient un ou plusieurs solvants qui sont choisis dans le groupe constitué par les citrates de trialkyle (de préférence le citrate de triéthyle, le citrate de triméthyle, le citrate de tripropyle, le citrate de triisopropyle, le citrate de tributyle, le citrate de triisobutyle ou le citrate de tri-sec-butyle), les phtalates de dialkyle (de préférence le phtalate de diméthyle, le phtalate de diéthyle ou le phtalate de dibutyle), le benzoate de benzyle, le myristate d'isopropyle et l'adipate de dioctyle, et/ou
    - est un produit choisi dans le groupe constitué par les lessives et les produits de nettoyage, les produits d'hygiène ou de soin, en particulier du domaine des soins corporels et des soins capillaires, de la cosmétique et du ménage, les parfums fins (parfums), les huiles de parfum, les produits à assainir l'air intérieur (en particulier bougies), les désodorisants, les produits de nettoyage, de traitement et/ou d'entretien de surfaces et de fibres textiles.
  9. Mélange selon la revendication 8, caractérisé par le fait que le mélange contient une, 2, 3, 4, 5, 6, 7, 8, 9, 10 autres substances odoriférantes ou plus qui ne sont pas de composés de la formule (I), et que la quantité totale des composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes se situe dans la plage allant de 0,0001 à 40 % en poids, de préférence dans la plage allant de 0,001 à 25 % en poids, respectivement par rapport au poids total du mélange.
  10. Mélange selon la revendication 8, caractérisé par le fait que le mélange contient un ou plusieurs solvants qui sont choisis dans le groupe des citrates de trialkyle, et que la quantité totale des composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes se situe dans la plage allant de 0,0001 à 40 % en poids, de préférence dans la plage allant de 0,001 à 25 % en poids, respectivement par rapport au poids total du mélange.
  11. Mélange selon la revendication 8 ou 10, caractérisé par le fait que le solvant ou l'un des solvants est choisi dans le groupe constitué par le citrate de triéthyle, le phtalate de diéthyle, le benzoate de benzyle, le myristate d'isopropyle et l'adipate de dioctyle.
  12. Mélange selon la revendication 8, caractérisé par le fait que le mélange est un produit choisi dans le groupe constitué par les lessives et les produits de nettoyage, les produits d'hygiène ou de soin, en particulier du domaine des soins corporels et des soins capillaires, de la cosmétique et du ménage, les parfums fins (parfums), les produits à assainir l'air intérieur (en particulier bougies), les désodorisants, les produits de nettoyage, de traitement et/ou d'entretien de surfaces et de fibres textiles, et que la quantité totale des composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes se situe dans la plage allant de 0,0001 à 5 % en poids, de préférence dans la plage allant de 0,001 à 2,5 % en poids, respectivement par rapport au poids total du produit.
  13. Procédé destiné à conférer et/ou à renforcer
    (i) une note olfactive de muguet
    ainsi que, le cas échéant, (ii)
    (ii)a) une, plusieurs ou toutes les notes olfactives choisies dans le groupe constitué par fleurie, fruitée, aqueuse, verte et aldéhyde
    et/ou
    (ii)b) une, plusieurs ou toutes les impressions choisies dans le groupe constitué par naturelle, fraîche, de soin, douce, chaude, complexe et rayonnante ;
    comprenant l'étape suivante :
    mélanger ou mettre en contact
    - un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes, de préférence un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications 3 à 5, ou
    - un mélange selon l'une quelconque des revendications 8 à 12 en une quantité sensoriellement efficace avec un produit.
  14. Procédé selon la revendication 13, destiné à pourvoir la peau, les cheveux, des surfaces ou fibres textiles
    (i) d'une note olfactive de muguet
    ainsi que, le cas échéant, (ii)
    (ii)a) d'une, de plusieurs ou de toutes les notes olfactives choisies dans le groupe constitué par fleurie, fruitée, aqueuse, verte et aldéhyde
    et/ou
    (ii)b) d'une, de plusieurs ou de toutes les impressions choisies dans le groupe constitué par naturelle, fraîche, de soin, douce, chaude, complexe et rayonnante ;
    comprenant les étapes suivantes :
    - fournir
    - un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications précédentes, de préférence un ou plusieurs composés de la formule (I) tels que définis dans l'une quelconque des revendications 3 à 5, ou
    - un mélange selon l'une quelconque des revendications 8 à 12,
    - appliquer le(s) composé(s) de la formule (I) ou bien le mélange ou le produit parfumé sur la peau, les cheveux, les surfaces ou les fibres textiles.
EP20110189681 2011-11-18 2011-11-18 Utilisation d'oxyacétaldéhydes comme parfums sentant le muguet Active EP2594626B1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019122236A1 (fr) 2017-12-21 2019-06-27 Firmenich Sa Procédé d'identification de modulateurs allostériques positifs pour des récepteurs odorants
WO2020127325A2 (fr) 2018-12-19 2020-06-25 Firmenich Sa Utilisation de composés volatils pour moduler la perception du muguet floral

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* Cited by examiner, † Cited by third party
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JP6720195B2 (ja) 2015-01-30 2020-07-08 ローディア ポリアミダ エ エスペシアリダデス エス．アー． 香料組成物およびエアケアデバイス
RU2719142C2 (ru) * 2015-02-02 2020-04-17 Джонсон энд Джонсон Консьюмер Инк. Парфюмерные композиции

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DE3811059A1 (de) * 1988-03-31 1989-10-12 Hoechst Ag Verfahren zur trennung von butanol und butoxyacetaldehyd
DE4021015A1 (de) * 1990-07-02 1992-01-09 Henkel Kgaa Oxyacetaldehyde
AT409129B (de) * 2000-07-05 2002-05-27 Dsm Fine Chem Austria Gmbh Verfahren zur herstellung von alkyl- oder aryloxyacetaldehyden
EP1201738A1 (fr) 2000-10-30 2002-05-02 Pfw Aroma Chemicals B.V. Composition parfumante contenant de la cyclohexadécanone
DE10308047A1 (de) * 2003-02-26 2004-09-09 Symrise Gmbh & Co. Kg 4-Cyclohexyl-2-butanol als Riechstoff
EP1857436A1 (fr) * 2006-05-19 2007-11-21 Kao Corporation, S.A. Précurseurs pour produits parfumants
GB0702017D0 (en) * 2007-02-02 2007-03-14 Quest Int Serv Bv Novel fragrance compounds
DE102008039417A1 (de) * 2008-08-13 2010-02-18 Eberhard-Karls-Universität Tübingen Universitätsklinikum Mittel zum Nachweis und zur Behandlung von Prostatazellen

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019122236A1 (fr) 2017-12-21 2019-06-27 Firmenich Sa Procédé d'identification de modulateurs allostériques positifs pour des récepteurs odorants
WO2020127325A2 (fr) 2018-12-19 2020-06-25 Firmenich Sa Utilisation de composés volatils pour moduler la perception du muguet floral

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